30450-62-5

Usage

Uses

Used in Organic Synthesis:
7-Nitro-1,2,3,4-tetrahydroquinoline is utilized as a key building block in organic synthesis for the creation of various complex organic molecules. Its presence in the synthesis process is crucial for the development of new pharmaceuticals and other chemical compounds.
Used in Pharmaceutical Research:
As a precursor in the synthesis of bioactive molecules, 7-Nitro-1,2,3,4-tetrahydroquinoline is employed in pharmaceutical research to explore its potential as a starting material for the development of new drugs with therapeutic applications.
Used in Fluorescent Probe Development:
7-Nitro-1,2,3,4-tetrahydroquinoline has been investigated for its potential use as a fluorescent probe for detecting biological molecules. Its fluorescent properties make it a candidate for applications in biochemistry and molecular biology, where the detection and tracking of specific biomolecules are essential.
Used in Research Applications:
Due to its unique structure and properties, 7-Nitro-1,2,3,4-tetrahydroquinoline is also used in various research applications, including the study of chemical reactions and the development of new methodologies in synthetic chemistry.

InChI:InChI=1/C9H10N2O2/c12-11(13)8-4-3-7-2-1-5-10-9(7)6-8/h3-4,6,10H,1-2,5H2

Upstream product

• 4169-19-1 1-acetyl-1,2,3,4-tetrahydroquinoline 
• 861609-66-7 2-(3-chloro-propyl)-5-nitro-aniline 
• 767-92-0 decahydroquinoline 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 40484-69-3 1-benzoyl-7-nitro-1,2,3,4-tetrahydro-quinoline 
• 861529-01-3 benzoic acid-[2-(3-chloro-propyl)-5-nitro-anilide] 
• 22774-77-2 N-allyl-(3-nitrophenyl)amine 
• 613-51-4 7-nitroquinoline 

Downstream Products

• 40484-66-0 N-acetyl-7-nitro-1,2,3,4-tetrahydroquinoline 
• 40484-69-3 1-benzoyl-7-nitro-1,2,3,4-tetrahydro-quinoline 
• 153856-89-4 7-amino-1,2,3,4-tetrahydroquinoline 
• 39275-18-8 1-methyl-7-nitro-1,2,3,4-tetrahydro-quinoline 

Relevant academic research and scientific papers

Controlling ground and excited state properties through ligand changes in ruthenium polypyridyl complexes

The capture and storage of solar energy requires chromophores that absorb light throughout the solar spectrum. We report here the synthesis, characterization, electrochemical, and photophysical properties of a series of Ru(II) polypyridyl complexes of the type [Ru(bpy)2(N-N)]2+ (bpy = 2,2-bipyridine; N-N is a bidentate polypyridyl ligand). In this series, the nature of the N-N ligand was altered, either through increased conjugation or incorporation of noncoordinating heteroatoms, as a way to use ligand electronic properties to tune redox potentials, absorption spectra, emission spectra, and excited state energies and lifetimes. Electrochemical measurements show that lowering the φ* orbitals on the N-N ligand results in more positive Ru3+/2+ redox potentials and more positive first ligand-based reduction potentials. The metal-to-ligand charge transfer absorptions of all of the new complexes are mostly red-shifted compared to Ru(bpy)32+ (λmax = 449 nm) with the lowest energy MLCT absorption appearing at λmax = 564 nm. Emission energies decrease from λmax = 650 nm to 885 nm across the series. One-mode Franck-Condon analysis of room-temperature emission spectra are used to calculate key excited state properties, including excited state redox potentials. The impacts of ligand changes on visible light absorption, excited state reduction potentials, and Ru3+/2+ potentials are assessed in the context of preparing low energy light absorbers for application in dye-sensitized photoelectrosynthesis cells.

Efficient and selective hydrogenation of quinolines over FeNiCu/MCM-41 catalyst at low temperature: Synergism of Fe-Ni and Ni-Cu alloys

The development of non-precious metal catalysts in heterogeneous catalytic processes is of great importance to the hydrogenation of quinolines for both theoretical and industrial applications. Herein, an effective non-precious metal catalyst, 58% Fe4Ni6Cu5/MCM-41, was developed to catalyze the hydrogenation of quinolines under the green and mild conditions, which can achieve 97.5% conversion and exceeding 98% selectivity to tetrahydroquinoline in solvent-free at low temperature of 50 °C. Moreover, the acceptable results of the reusability and gram scale-up experiments proved an industrial application potential of the as-prepared catalyst. Meanwhile, in cyclohexane system, 58% Fe4Ni6Cu5/MCM-41 catalyst can further realize a higher activity of the hydrogenation at a lower temperature of 40 °C, achieving 98.2% conversion and 98% selectivity to tetrahydroquinoline. The existence of Fe-Ni and Ni-Cu alloys in Fe4Ni6Cu5/MCM-41 catalyst was demonstrated by TEM, XRD, XPS, H2-TPD, and Raman spectroscopy. And, Fe-Ni and Ni-Cu alloys can be well dispersed onto MCM-41 molecular sieves. For Fe4Ni6Cu5/MCM-41 catalyst, quinoline molecules can be adsorbed by Fe3+ species on the surface of Fe-Ni alloy through the coordination, while hydrogen molecules can be adsorbed and activated by Ni-Cu alloy. Under the synergism of Fe-Ni and Ni-Cu alloys, the highly effective and selective hydrogenation of quinolines was achieved at low temperature and in solvent-free system. The present approach offers a prospective idea for building non-precious metal catalysts to realize the effective hydrogenation of N-heterocyclic compounds under mild conditions.

Development of versatile and potent monoquaternary reactivators of acetylcholinesterase

To date, the only treatments developed for poisoning by organophosphorus compounds, the most toxic chemical weapons of mass destruction, have exhibited limited efficacy and versatility. The available causal antidotes are based on reactivation of the enzyme acetylcholinesterase (AChE), which is rapidly and pseudo-irreversibly inhibited by these agents. In this study, we developed a novel series of monoquaternary reactivators combining permanently charged moieties tethered to position 6- of 3-hydroxypyridine-2-aldoxime reactivating subunit. Highlighted representatives (21, 24, and 27; also coded as K1371, K1374, and K1375, respectively) that contained 1-phenylisoquinolinium, 7-amino-1-phenylisoquinolinium and 4-carbamoylpyridinium moieties?as peripheral anionic site ligands, respectively, showed efficacy superior or comparable to that of the clinically used standards. More importantly, these reactivators exhibited wide-spectrum efficacy and were minutely investigated via determination of their reactivation kinetics in parallel with molecular dynamics simulations to study their mechanisms of reactivation of the tabun-inhibited AChE conjugate. To further confirm the potential applicability of these candidates, a mouse in vivo assay was conducted. While K1375 had the lowest acute toxicity and the most suitable pharmacokinetic profile, the oxime K1374 with delayed elimination half-life was the most effective in ameliorating the signs of tabun toxicity. Moreover, both in vitro and in vivo, the versatility of the agents was substantially superior to that of clinically used standards. Their high efficacy and broad-spectrum capability make K1374 and K1375 promising candidates that should be further investigated for their potential as nerve agents and insecticide antidotes.

Discovery of Benzopyridone-Based Transient Receptor Potential Vanilloid 1 Agonists and Antagonists and the Structural Elucidation of Their Activity Shift

Among a series of benzopyridone-based scaffolds investigated as human transient receptor potential vanilloid 1 (TRPV1) ligands, two isomeric benzopyridone scaffolds demonstrated a consistent and distinctive functional profile in which 2-oxo-1,2-dihydroquinolin-5-yl analogues (e.g., 2) displayed high affinity and potent antagonism, whereas 1-oxo-1,2-dihydroisoquinolin-5-yl analogues (e.g., 3) showed full agonism with high potency. Our computational models provide insight into the agonist-antagonist boundary of the analogues suggesting that the Arg557 residue in the S4-S5 linker might be important for sensing the agonist binding and transmitting signals. These results provide structural insights into the TRPV1 and the protein-ligand interactions at a molecular level.

Catalytic-Type Excited-State N?H Proton-Transfer Reaction in 7-Aminoquinoline and Its Derivatives

7-Aminoquinoline (7AQ) and various amino derivatives thereof (-NHR) have been strategically designed and synthesized to study their excited-state proton-transfer (ESPT) properties. Due to the large separation between the proton donor -NHR and the acceptor

Ordered Porous Nitrogen-Doped Carbon Matrix with Atomically Dispersed Cobalt Sites as an Efficient Catalyst for Dehydrogenation and Transfer Hydrogenation of N-Heterocycles

Single-atom catalysts (SACs) have been explored widely as potential substitutes for homogeneous catalysts. Isolated cobalt single-atom sites were stabilized on an ordered porous nitrogen-doped carbon matrix (ISAS-Co/OPNC). ISAS-Co/OPNC is a highly efficient catalyst for acceptorless dehydrogenation of N-heterocycles to release H2. ISAS-Co/OPNC also exhibits excellent catalytic activity for the reverse transfer hydrogenation (or hydrogenation) of N-heterocycles to store H2, using formic acid or external hydrogen as a hydrogen source. The catalytic performance of ISAS-Co/OPNC in both reactions surpasses previously reported homogeneous and heterogeneous precious-metal catalysts. The reaction mechanisms are systematically investigated using first-principles calculations and it is suggested that the Eley–Rideal mechanism is dominant.

N-sulfonylated tetrahydroquinolines and related bicyclic compounds for inhibition of RORγ activity and the treatment of disease

The invention provides tetrahydroquinoline and related compounds, pharmaceutical compositions, methods of inhibiting RORγ activity, reducing the amount of IL-17 in a subject, and treating immune disorders and inflammatory disorders using such tetrahydroqu

Ezrin inhibitors and methods of making and using

The invention encompasses compound and pharmaceutical composition comprising the compound of the following Formula (I): or pharmaceutically acceptable salts or prodrugs thereof, that are useful for inhibiting ezrin protein in a cell or for inhibiting the growth of a cancer cell.

Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases

The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

Selective anti-markovnikov cyclization and hydrofluorination reaction in superacid HF/SbF5: A tool in the design of nitrogen-containing (fluorinated) polycyclic systems

The selective synthesis of tetrahydroquinolines and fluorinated arylamines was performed in superacid HF/SbF5 through a superelectrophilic ammonium-carbenium activation process. This anti-Markovnikov oriented reaction was applied to the straightforward synthesis of highly valued (fluorinated) nitrogen-containing heterocyclic compounds.